Water-insoluble azo dyestuffs and material dyed therewith



Patented May 19, 193i UNITED STATES PATENT OFFICE I KARL BECK AND IHIEJRJBERG? KRACKER. OF FRANKIEORT-ON-THE-MAIN-HOGHST, GER- MANY, ASSIGNORS T GENERAL ANILINE WORKS, INC., OF NEW YORK, N. Y., A. COR- I'ORATION OF DELAWARE WATER-IN SOLUBLE .AZO DYESTUFFS AND MATERIAL DYED THEREWITH llo Drawing. Application filed December 5, 1928, Serial No. 324,052, and in Germany December 17, 1927.

Our present invention relates to new waterout or by centrifugating it and dyed for insoluble azo dyestuffs and material dyed one mlnute in the dlazo solutlon. The dyed therewith.

We have found that dyestuffs of excellent fastness are obtained by coupling a diazo compound of a dihalogenated 2-amino-l-toluene containing one halogen atomin 6zposition and the other in 3: or 5: position of the general formula:

CHa

wherein both the Xs stand for halogen, with an arylamide of 2.3-hydroxynaphthoic acid.

The dyestuiis obtained by our invention correspond to the general formula:

yarn i s then thoroughly rinsed, soaped at boiling temperature and again rinsed.

The grounding liquor is prepared as follows of 2.3- hyclroxynaphthoic acid-2'.5-di1nethoxy-1- anilid cc. of sodium Turkey red oil of strength 1 liter.

The developing bath is prepared as follows:

1 liter.

The

of 5.6-dichl0r0-2-arnino-l-t0luene are made into a paste with I of hydrochloric acid of 22 B, and a small quantity of water;

of dissolved sodium nitrite and some ice are gradually added. After the diazotization is complete, the solution is neutralized with of sodium acetate and the whole is made up to dyestuii has the formula:

p O CH] OQNHQ The dyeing has a vivid, bluish-red shade. 2. The grounding liquor is prepared as follows:

9 cc. 11.25 cc.

1 liter.

of 12&3-11vdroxynaphthoic acid-4'-chloro-2-anisi- The developing bath is prepared as follows:

4.4 g. of 5-bromo-G-chlor0-2-amino-1-to1uene with a small quantity of water and 9 cc. of sodium Turkey red Oil of 50% strength 11.25 cc. of caustic soda solution of 34 B are dissolved in hot water; the solution is cooled to about 50 C. and c. of formaldehyde of 30% strength are added and the whole is made up to 1 liter.

The dyeing has a Vivid scarlet shade of good fastness properties. 7

3. 717.6 parts of 8.6-dichloro-2-amino-ltoluene are diazotized in known manner with Shade of the dyestufl and the lake obtained thereof, respectively Diazo compound from Combined with 5.6-dich1oro-2a1ninol-toluene. 5.6-diehloro-2a-nino- 2.3-hydroxynaphthoic Bluish-red.

para-anisidide.

l-toluene.

.5.6-dich1oro-2-aminol-toluenei 5.6-dichloro-2-aminol-toluene. 5.6-dichloro-2-aminol-toluene. 5.6-diehloro-2-aminol-toluene. 5-bromo-6-eh1oro-2- amino-l-toluene. 5-bromo-6-chloro-2- amino-l-toluene. 5-bromo-6-chloro-2- amino-l-toluene.

2.3-hydroxynaphthoic 0rthoanisidide. 2.3-hydroxynaphthoic 2.3-hydroxynaphthoic 2.3-hydroxynaphthoic 2-chloto-4-anisidide.

2.3-hydroxynaphthoic a-naphthalide.

2.3-hydroxynaphthoic para-anisidide. ZB-hydroxynaphthoic acid acid

2.3-hydroxynaphthoic a-naphthalide.

acid

Bluish-red.

Vivid scarlet.

Bluish-red.

Brick-red.

Claret-red.

Bluish-red. Bluish-red.

Claret-red.

lVe claim 1. As new products, the water-insoluble azo dyestuffs of the following formula:

CO.NH. aryl wherein both the Xs stand for equal or different halogen atoms, of which the one not standing in a fixed position may'stand in 3 or in 5 position and wherein the aryl residue may be substituted or not, but must not'contain any free sulfonicor carboxylic groups, dyeing red shades fast to light.

2. As new products, the water-insoluble azo dyestuffs of the following formula:

(.lHz X wherein both the Xs stand for equal or. different halogen atoms, and wherein the aryl residue may be substituted or not but must not contain any free sulfonicor carboxylic groups, dyeing red shades fast to light. .-I

3. As new products, the water-insoluble azo dyestuifs of the following formula:

CO.NH. aryl oo.NH'. aryl wherein X stands for C1 or-Br and wherein the aryl residue may be substituted or not but must not contain any free sulfonic or carboxylic groups, dyeing red shades fast to light. I v

4. As new products, the water-insoluble azo dyestuffs of. the following formula:

wherein the aryl residue may be substituted or not, but must not contain any free sulfonicor carboxylic groups, dyeing red 7:

shades fast to light. 1

5. As new products, the water-insoluble azo dyestuffs of the following formula:

l wherein both the Xs stand for equal or differen't halogen atoms, and wherein Y stands for hydrogen or the OCH -group, dyeing red shades fast to light.

6. As new products, the water-insoluble azo dyestuffs of the following formula:

OCH;

OO.NH

Y wherein X stands for C1 or Br and Y stands for hydrogen or the ()CH -group, dyeing red shades fast to light.

7. As new products, the Water-insoluble azo dyestuffs of the following formula:

3 4 N=N 2 5 Cl OCH;

Y wherein Y stands for hydrogen or the OCH -group, dyeing red shades fast to light.

8. As a new product, the water-insoluble azo dyestulf of the following formula:

3 4 N=N 2 6 O1 OCH:

OO.NH

tures.

KARL BECK. HERBERT KRACKER. 

